41661

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

absolute, over molecular sieve (H₂O ≤0.05%), ≥99.0% (GC)

• Synonym(s): 1,3-Dimethyl-2-oxohexahydropyrimidine, N,N′-Dimethylpropylene urea, DMPU
• Empirical Formula (Hill Notation): C₆H₁₂N₂O
• CAS Number: 7226-23-5
• Molecular Weight: 128.17
• Beilstein: 110562
• EC Number: 230-625-6
• MDL number: MFCD00006550
• UNSPSC Code: 12352115
• PubChem Substance ID: 57650056
• NACRES: NA.22

Properties

• grade: absolute
• Quality Level: 200
• Assay: ≥99.0% (GC)
• form: liquid
• quality: over molecular sieve (H₂O ≤0.05%)
• refractive index: n20/D 1.488 (lit.); n20/D 1.489
• bp: 146 °C/44 mmHg (lit.)
• density: 1.06 g/mL at 25 °C (lit.)
• SMILES string: CN1CCCN(C)C1=O
• InChI: 1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3
• InChI key: GUVUOGQBMYCBQP-UHFFFAOYSA-N

Description

Application

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) can be used as a:

• Solvent in the synthesis of 1-aryl-3,4,5-substituted pyrazoles by cyclocondensation of 1,3-diketones with arylhydrazine hydrochlorides.
• Chelating solvent in the trifluoromethylation of activated and non-activated halogenated double bonds.
• Ligand in ortho-alkylation of secondary benzamide catalyzed by cobalt.

Other Notes

Aprotic, dipolar solvent, which is an excellent replacement of the carcinogenic HMPA as cosolvent for highly reactive nucleophiles and bases. High Z-selectivity in enolate formation; DMPU was shown to be non-mutagenic and safe.

Safety Information

• Pictograms: GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H318,H361f
• Precautionary Statements: P202 - P264 - P280 - P301 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 1
• Flash Point(F): 249.8 °F - closed cup
• Flash Point(C): 121 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves